Synthesis of Novel Functionalized<b><i>N</i></b>-Tosylaldimines

Wynne, James H.; Price, Stacy E.; Rorer, Jeffrey R.; Stalick, Wayne M.

doi:10.1081/scc-120015720

Cited by 40 publications

(15 citation statements)

References 24 publications

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“…Condensation of benzaldehyde with the p-toluenesulfonamide in appropriate solvent was carried out under reflux conditions (Table 1, entry 2). 26 The final product was obtained in 2 hrs of heating with low yields (15%). Next, we screened AlCl 3 under similar conditions.…”

Section: Resultsmentioning

confidence: 99%

A novel method for the synthesis of N-sulfonyl aldimines using AlCl3 under solvent-free conditions (SFC)

Sharghi¹,

Hosseini‐Sarvari²,

Ebrahimpourmoghaddam³

2007

Arkivoc

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Section: Resultsmentioning

confidence: 99%

A novel method for the synthesis of N-sulfonyl aldimines using AlCl3 under solvent-free conditions (SFC)

Sharghi¹,

Hosseini‐Sarvari²,

Ebrahimpourmoghaddam³

2007

Arkivoc

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“…THF was dried and distilled prior to use. HfBn 4 [17] and all the imines [20] were prepared according to reported methods. Other chemicals were used as obtained from commercial sources without further purification.…”

Section: Methodsmentioning

confidence: 99%

Tetrabenzylhafnium as a New Organometallic Reagent for Imine Addition Resulting in α‐Branched Amines

Mei

Han

et al. 2011

Eur J Org Chem

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“…39 Imines 1f and 1n by a modification of the method of Proctor, 41 and imines 1b , 1e by the method of Stalick. 40 …”

Section: Methodsmentioning

confidence: 99%

Synthesis ofcis-C-Iodo-N-Tosyl-Aziridines using Diiodomethyllithium: Reaction Optimization, Product Scope and Stability, and a Protocol for Selection of Stationary Phase for Chromatography

et al. 2013

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The preparation of C-iodo-N-Ts-aziridines with excellent cis-diastereoselectivity has been achieved in high yields by the addition of diiodomethyllithium to N-tosylimines and N-tosylimine–HSO2Tol adducts. This addition-cyclization protocol successfully provided a wide range of cis-iodoaziridines, including the first examples of alkyl-substituted iodoaziridines, with the reaction tolerating both aryl imines and alkyl imines. An ortho-chlorophenyl imine afforded a β-amino gem-diiodide under the optimized reaction conditions due to a postulated coordinated intermediate preventing cyclization. An effective protocol to assess the stability of the sensitive iodoaziridine functional group to chromatography was also developed. As a result of the judicious choice of stationary phase, the iodoaziridines could be purified by column chromatography; the use of deactivated basic alumina (activity IV) afforded high yield and purity. Rearrangements of electron-rich aryl-iodoaziridines have been promoted, selectively affording either novel α-iodo-N-Ts-imines or α-iodo-aldehydes in high yield.

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Synthesis of Novel FunctionalizedN-Tosylaldimines

Cited by 40 publications

References 24 publications

A novel method for the synthesis of N-sulfonyl aldimines using AlCl3 under solvent-free conditions (SFC)

A novel method for the synthesis of N-sulfonyl aldimines using AlCl3 under solvent-free conditions (SFC)

Tetrabenzylhafnium as a New Organometallic Reagent for Imine Addition Resulting in α‐Branched Amines

Synthesis ofcis-C-Iodo-N-Tosyl-Aziridines using Diiodomethyllithium: Reaction Optimization, Product Scope and Stability, and a Protocol for Selection of Stationary Phase for Chromatography

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